ID: ALA583611

Max Phase: Preclinical

Molecular Formula: C25H42O4

Molecular Weight: 406.61

Molecule Type: Small molecule

Representations

Synonyms (1): 23(S)-Methyl-Chenodeoxycholic Acid
Synonyms from Alternative Forms(1):

Canonical SMILES:  C[C@H](C[C@H](C)C(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

Standard InChI:  InChI=1S/C25H42O4/c1-14(11-15(2)23(28)29)18-5-6-19-22-20(8-10-25(18,19)4)24(3)9-7-17(26)12-16(24)13-21(22)27/h14-22,26-27H,5-13H2,1-4H3,(H,28,29)/t14-,15+,16+,17-,18-,19+,20+,21-,22+,24+,25-/m1/s1

Standard InChI Key:  XMIXAXLPZCFFCG-BQWNBIDXSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 406.61

Molecular Weight (Monoisotopic): 406.3083

AlogP: 4.72

#Rotatable Bonds: 4

Polar Surface Area: 77.76

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 4.60

CX Basic pKa:

CX LogP: 4.26

CX LogD: 1.53

Aromatic Rings: 0

Heavy Atoms: 29

QED Weighted: 0.63

Np Likeness Score: 2.47

References

1. Pellicciari R, Gioiello A, Macchiarulo A, Thomas C, Rosatelli E, Natalini B, Sardella R, Pruzanski M, Roda A, Pastorini E, Schoonjans K, Auwerx J..  (2009)  Discovery of 6alpha-ethyl-23(S)-methylcholic acid (S-EMCA, INT-777) as a potent and selective agonist for the TGR5 receptor, a novel target for diabesity.,  52  (24): [PMID:20014870] [10.1021/jm901390p]

2. Yu DD, Sousa KM, Mattern DL, Wagner J, Fu X, Vaidehi N, Forman BM, Huang W..  (2015)  Stereoselective synthesis, biological evaluation, and modeling of novel bile acid-derived G-protein coupled bile acid receptor 1 (GP-BAR1, TGR5) agonists.,  23  (7): [PMID:25735208] [10.1016/j.bmc.2015.01.048]

3. Xu Y..  (2016)  Recent Progress on Bile Acid Receptor Modulators for Treatment of Metabolic Diseases.,  59  (14): [PMID:26878262] [10.1021/acs.jmedchem.5b00342]

Source

Source(1):

• Scientific Literature